5'-O-benzoyl-3'-O-(N,N-diisopropylmethylphosphoramidyl)-4'-[(2-methyl-2-(2-iodophenyl)propylthio)carbonyl]thymidine

Base Information

Chemical Name:5'-O-benzoyl-3'-O-(N,N-diisopropylmethylphosphoramidyl)-4'-[(2-methyl-2-(2-iodophenyl)propylthio)carbonyl]thymidine
CAS No.:201672-25-5
Molecular Formula:C₃₅H₄₅IN₃O₈PS
Molecular Weight:825.702
Hs Code.:

Synonyms:5'-O-benzoyl-3'-O-(N,N-diisopropylmethylphosphoramidyl)-4'-[(2-methyl-2-(2-iodophenyl)propylthio)carbonyl]thymidine

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Chemical Property of 5'-O-benzoyl-3'-O-(N,N-diisopropylmethylphosphoramidyl)-4'-[(2-methyl-2-(2-iodophenyl)propylthio)carbonyl]thymidine

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Technology Process of 5'-O-benzoyl-3'-O-(N,N-diisopropylmethylphosphoramidyl)-4'-[(2-methyl-2-(2-iodophenyl)propylthio)carbonyl]thymidine

There total 6 articles about 5'-O-benzoyl-3'-O-(N,N-diisopropylmethylphosphoramidyl)-4'-[(2-methyl-2-(2-iodophenyl)propylthio)carbonyl]thymidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.5%

: N,N-diisopropyl-O-methylphosphonamidic chloride

: 201672-23-3
5'-O-benzoyl-4'-[(2-methyl-2-(2-iodophenyl)propylthio)carbonyl]thymidine

: 201672-25-5
5'-O-benzoyl-3'-O-(N,N-diisopropylmethylphosphoramidyl)-4'-[(2-methyl-2-(2-iodophenyl)propylthio)carbonyl]thymidine

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 12h;
DOI:10.1016/S0040-4020(97)10262-9

Reference yield:

: 177748-67-3
2-(2-iodophenyl)-2-methylpropanethiol

: 201672-25-5
5'-O-benzoyl-3'-O-(N,N-diisopropylmethylphosphoramidyl)-4'-[(2-methyl-2-(2-iodophenyl)propylthio)carbonyl]thymidine

Guidance literature:: Multi-step reaction with 3 steps

1: 700 mg / DMAP / CH₂Cl₂ / 12 h / 20 °C

2: 93 percent / acetic acid; TBAF / tetrahydrofuran / 18 h

3: 88.5 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 12 h

With dmap; tetrabutyl ammonium fluoride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Acylation / 2: desilylation / 3: phosphoroamidation;
DOI:10.1016/S0040-4020(97)10262-9

Reference yield:

: 201672-12-0
(2R,3S,5R)-2-Benzoyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carboxylic acid tert-butyl ester

: 201672-25-5
5'-O-benzoyl-3'-O-(N,N-diisopropylmethylphosphoramidyl)-4'-[(2-methyl-2-(2-iodophenyl)propylthio)carbonyl]thymidine

Guidance literature:: Multi-step reaction with 5 steps

1: trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 - 20 °C

2: 1,1-dichloromethyl methyl ether / benzene / 1 h / Heating

3: 700 mg / DMAP / CH₂Cl₂ / 12 h / 20 °C

4: 93 percent / acetic acid; TBAF / tetrahydrofuran / 18 h

5: 88.5 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 12 h

With dmap; Dichloromethyl methyl ether; tetrabutyl ammonium fluoride; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; benzene; 1: acidolysis / 2: Chlorination / 3: Acylation / 4: desilylation / 5: phosphoroamidation;
DOI:10.1016/S0040-4020(97)10262-9